The first time doing it with someone in this line of work was with Courtney. I was a hobbyist virgin. The combination of nervous energy and excitement, and her being her, will never be duplicated.
The other time was with a different girl when she decided she didn't do F/S on the first date. The ultimate GFE! But she would allow you to pleasure her any other way you'd like. It was so much fun to realize that pleasuring her could be soooo much more mind bending than focusing on me. Never would'a thunk it.
The time I helped, through extended DATY, a young provider reach what she claimed was her first orgasm, outsid of masturbation. While I may be naive, her reaction made me believe her. In any event the enthusiastic cowgirl and miss that followed taught me that providing pleasure is the surest way of receiving pleasure.
Once I shot it right up her nose, by accident, and she laughed her cute little butt off. 
I would also pick two experiences. Both times had similarities in the sense that they were the second time I had seen each lady (one in the Twin Cities and one in Canada.) In both cases, the first date with each of them had been great, but the second date was completely different, and incredible.
Somehow, the fact that we knew each other a little bit, but were still somewhat strangers, created the right tension between us. This created a situation, at least for me, where every touch was so intense, or so tender, that neither experience can be described in words.
I had seen one Lady several times, and we had gotten to a point where we both enjoyed each other’s company on several levels. One evening I had arranged for three hours with her for her birthday and took her out for a long dinner at her favorite restaurant. Afterwards I brought her to my hotel to give her a present and then to drive her home.
We never did leave the room until late the next morning, and among all the very sensual, very pleasant activities, the most memorable was holding her as she fell asleep.
Well, when the arm falls asleep it might not be enjoyable any more, but the agony of deciding whether to put up with it or risk waking her can still be “memorable".
I am looking forward to my most memorable moment when I have a double with you and Nicole in a couple weeks. I have been with both of you individually and had great times, so I am sure that my first double will certainly be right there.
My most memorable night was with a tantra teacher in California. I had scheduled an hour to learn more about the art of holding back. Well she was a sweetheart in the woods that kept me on the edge for hours. Yes I have to admit I slip up once or twice but she made it all right again. Five hours later I finally had to leave due to a business appointment I had elsewhere.
Most providers look to get it over with as quickly as possible, she worked to make the pleasure last as long as possible.
My most memorable time was when the condom came off, sure killed the moment. I hadn't cum yet but we both were scared as hell. Another memorable time was with someone who squirts, always been a fantasy of mine.
So many to narrow it down to just one...
But if I had to choose, it was several years ago when a provider who is my good friend brought two other girls over with her for my birthday. [No guys, it wasn't a freebie!]
The three of them were dressed to kill and after some champagne toasts, they took turns sitting on my face and fed me all the birthday cake (daty) I could eat. Actually I could have eaten a lot more, but they had to eventually leave.
Hmmm...I remember this hottie in Philly, redhead as I remember...had her hair in pigtails, was totally casual.
Yeah, that was my best time, hands down, cock up...
My most memorable time in the hobby was a two-hour doubles session with you and Nicole(aka Sexy-Curves). I can still close my eyes and remember what a great time it was. An evil smile appears on my face just thinking about it.
Having experienced it once, you know it will be something that we will be doing again and again.
Thanks to you and Nicole for the memories.
Ken
So Shaye, what was your most memorable session??
Inquiring minds want to know.
Ken
